How can I get my music files back when they are no longer on the computer?

So the problem I am having is that I cannot play songs on the playlist because "the file cannot be located" error.  I checked the iTunes media folder and they weren't there. I searched my whole computer and they still could not be found.
The story behind the problem is that I pretty sure all the songs I am having troubles with were ones I purchased on my iPod Touch itself. Several months ago when I plugged my iPod into the computer so it could sync ( my iPod is old and can't connect to the WiFi anymore forcing me to buy songs on my computer again.) The songs purchased on my iPod showed up on my playlist on my computer but they had the "!" next to them and they were no longer on my iPod and when I tried to get them back on I got the "cannot be located" error. I then checked the iTunes music folder again and the only songs there were songs I purchased on my computer.
I am extremely frustrated. When I go to the iTunes store under "Purchases" they all show up however there is no way for me to download them again onto my computer because the "download" button cannot be clicked on because I am assuming it thinks the songs are already on the computer, but I know they aren't. I tried organizing my songs option and that didn't do anything.
Is there any way to download them again? Or at least tell the iTunes store that they aren't located on my computer anymore so I can download them again?
If I lost hundreds of dollars of music because the iTunes software is a piece a ****...

You might want to post this question to the iTunes Windows forum rather than the iPod forum - try iTunes for Windows
Just a note of encouragement - I doubt very much you've lost your music - they remember what you've purchased forever and as long as the content is still on the iTunes store you should never loose anything (however sometimes content is removed from the store for various reasons and in that cause if you don't have a local copy on your iTunes library it is not recoverable - but that issue is relatively infrequent) - it's just a question of why iTunes won't let you download it again. good luck...

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